21244-59-7Relevant academic research and scientific papers
Hit-to-lead optimization of novel benzimidazole phenylacetamides as broad spectrum trypanosomacides
Avery, Vicky M.,Baell, Jonathan,McNamara, Nicole,Rahmani, Raphael,Sykes, Melissa L.
supporting information, p. 685 - 695 (2020/08/24)
Trypanosoma cruzi and Trypanosoma brucei are the parasitic causative agents of Chagas disease and human African trypanosomiasis (HAT), respectively. The drugs currently used to treat these diseases are not efficacious against all stages and/or parasite sub-species, often displaying side effects. Herein, we report the SAR exploration of a novel hit, 2-(4-chlorophenyl)-N-(1-propyl-1H-benzimidazol-2-yl)acetamide previously identified from high throughput screens against T. cruzi, Trypanosoma brucei brucei and Leishmania donovani. An informative set of analogues was synthesized incorporating key modifications of the scaffold resulting in improved potency whilst the majority of compounds retained low cytotoxicity against H9c2 and HEK293 cell lines. The SAR observed against T. cruzi broadly matches that observed against T.b. brucei, suggesting the possibility for a broad-spectrum candidate. This class of compounds therefore warrants further investigation towards development as a treatment for Chagas disease and HAT. This journal is
Synthesis and anti-inflammatory evaluation of novel benzimidazole and imidazopyridine derivatives
Chen, Gaozhi,Liu, Zhiguo,Zhang, Yali,Shan, Xiaoou,Jiang, Lili,Zhao, Yunjie,He, Wenfei,Feng, Zhiguo,Yang, Shulin,Liang, Guang
supporting information, p. 69 - 74 (2013/03/14)
Sepsis, an acute inflammatory disease, remains the most common cause of death in intensive care units. A series of benzimidazole and imidazopyridine derivatives were synthesized and screened for anti-inflammatory activities, and the imidazopyridine series showed excellent inhibition of the expression of inflammatory cytokines in LPS-stimulated macrophages. Compounds X10, X12, X13, X14, and X15 inhibited TNF-α and IL-6 release in a dose-dependent manner, and X12 showed no cytotoxicity in hepatic cells. Furthermore, X12 exhibited a significant protection against LPS-induced septic death in mouse models. Together, these data present a series of new imidazopyridines with potential therapeutic effects in acute inflammatory diseases.
A 'one-pot' phase transfer alkylation/hydrolysis of o-nitrotrifluoroacetanilides. A convenient route to N-alkyl o-phenylenediamines
Brown, Samuel A.,Rizzo, Carmelo J.
, p. 4065 - 4080 (2007/10/03)
A variety of o-nitrotrifluoroacetanilides undergo a one-pot alkylation/hydrolysis to give N-alkyl o-nitroanilines in 40-94% yield. Dimethylsulfate, benzyl bromide and 1-bromo-propane were used as the electrophiles.
Synthesis of 1-Alkoxy-2-Alkyl-Benzimidazoles from 2-Nitroanilines via Tandem N-Alkylation-Cyclization-O-Alkylation
Gardiner, John M.,Loyns, Colin R.,Schwalbe, Carl H.,Barrett, Garry C.,Lowe, Philip R.
, p. 4101 - 4110 (2007/10/02)
Substituted 2-nitroanilines react with benzylic, allyl and alkyl halides to give 2-aryl-1-benzyloxy-, 1-allyloxy-2-vinyl- and 1-alkoxy-2-alkyl-benzimidazoles, in a one-pot cascade process involving 1-alkylation-cyclization-O-alkylation. 2-Aryl-1-benzyloxy- and 1-allyloxy-2-vinyl- derivatives are obtained in high yields (79-98percent), while with simple alkyl halides, yields of the benzimidazoles are substrate dependent.An X-ray crystal structure of 2,4-dimethyl-1-ethoxybenzimidazole is presented.
Design and syntheses of a series of novel serotonin3 antagonists
Hori,Suzuki,Yamamoto,Nakajima,Ozaki,Ohtaka
, p. 1832 - 1841 (2007/10/02)
From a structural comparison study between serotonin and serotonin3 (5- HT3) antagonists using a two-dimensional grid template composed of regular hexagons, we deduced structural modification patterns from agonists to antagonists, an
